The Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
87(21), P. 14840 - 14845
Published: Oct. 21, 2022
Herein,
we
disclose
a
strategy
to
realize
α,β-difunctionalization
and
C–N
bond
cleavage
of
saturated
amines
with
benzo[c]isoxazoles
via
B(C6F5)3-catalyzed
consecutive
hydrogen-borrowing
[4
+
2]
cycloaddition
followed
by
process.
In
general,
the
reactions
proceed
efficiently
in
absence
any
oxidant
metal
catalyst
afford
broad
range
quinoline
derivatives
starting
from
easily
accessible
substrates
an
atom-economical
manner.
Chemical Science,
Journal Year:
2021,
Volume and Issue:
13(3), P. 775 - 780
Published: Dec. 20, 2021
An
unprecedented
redox-neutral
annulation
reaction
of
tertiary
anilines
with
electron-deficient
alkynes
was
developed
that
proceeds
through
a
cascade
Friedel-Crafts
alkylation/[1,5]-hydride
transfer/Mannich
cyclization
sequence.
Under
B(C6F5)3
catalysis,
range
functionalized
1,2,3,4-tetrahydroquinolines
were
facilely
constructed
in
moderate
to
good
yields
exclusive
3,4-anti-stereochemistry.
The
commercial
availability
the
catalyst
and
high
atom
step
economy
procedure,
together
metal-free
external
oxidant-free
conditions,
make
this
an
attractive
method
organic
synthesis.
Organic & Biomolecular Chemistry,
Journal Year:
2023,
Volume and Issue:
21(13), P. 2709 - 2714
Published: Jan. 1, 2023
We
report
a
new
gate
for
changing
photo
inactive
compounds
into
photocatalysts
with
easy
operation,
good
tolerance
of
functional
groups,
and
considerable
yield.
demonstrate
the
synthesis
natural
products
Azacephalandole
A
Cephalandole
in
high
yields.
Organic Letters,
Journal Year:
2021,
Volume and Issue:
23(16), P. 6367 - 6371
Published: July 29, 2021
A
simple
one-pot
procedure
enables
the
sequential,
regioselective,
and
diastereoselective
introduction
of
same
or
two
different
substituents
to
α-
α′-positions
unprotected
azacycles.
Aryl,
alkyl,
alkenyl
are
introduced
via
their
corresponding
organolithium
compounds.
The
scope
this
transformation
includes
pyrrolidines,
piperidines,
azepanes,
piperazines.
Asian Journal of Organic Chemistry,
Journal Year:
2022,
Volume and Issue:
12(2)
Published: Oct. 19, 2022
Abstract
C−H
bond
functionalization
is
one
of
the
most
efficient
strategies
for
rapid
synthesis
cyclic
amines
containing
substituents
in
ring,
which
are
core
structures
many
bioactive
molecules.
However,
it
much
more
challenging
to
perform
this
strategy
on
remote
bonds
than
α
‐C−H
amines.
This
review
provides
a
comprehensive
overview
transition
metal‐free
methods
amines,
complementary
relying
metal
catalysis.
Selected
substrate
scope
and
discussion
reaction
mechanism
given
when
necessary.
Synthesis,
Journal Year:
2021,
Volume and Issue:
53(17), P. 2947 - 2960
Published: April 15, 2021
Abstract
Reactions
that
take
place
via
C–H
functionalization
are
valuable
tools
in
organic
synthesis
because
they
can
be
used
for
the
of
target
compounds
and
late-stage
bioactive
compounds.
Among
these,
non-directed
C(sp3)–H
reactions
saturated
nitrogen-containing
heterocycles
have
been
developed
recent
years.
However,
most
these
lead
to
at
α-position
relative
heteroatom,
β-
or
γ-positions
limited
since
bonds
stronger
less
electron-rich.
Hence,
this
review,
we
will
discuss
γ-C(sp3)–H
heterocycles,
which
interest
medicinal
chemists.
These
methods
attractive
order
avoid
pre-functionalization
substrates,
reduce
number
synthetic
steps
formation
byproducts.
Such
divided
into
enamine-intermediate-mediated
processes
other
reaction
types
described
review.
1
Introduction
2
Non-Directed
β-C(sp3)–H
Functionalization
Saturated
Nitrogen-Containing
Heterocycles
an
Enamine
Intermediate
2.1
under
Acidic,
Basic
Thermal
Conditions
2.2
Oxidative
2.3
Redox-Neutral
3
Strategies
Excluding
Examples
Proceeding
4
Summary
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(34), P. 6335 - 6340
Published: Aug. 19, 2022
Herein,
we
describe
the
dual
C(sp3)–H
bond
functionalization
of
a
tertiary
amine
through
hydride-transfer-induced
dehydrogenation,
followed
by
cycloaddition,
using
an
easily
preparable
diazoester
as
new
type
hydride-acceptor
precursor
under
mild,
redox-neutral
conditions.
With
carbene
hydrogen
acceptor,
this
method
was
demonstrated
preparation
broad
range
functionalized
isoxazoldines
in
moderate
to
good
yields.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(42), P. 7839 - 7844
Published: Oct. 20, 2022
Herein
we
describe
a
convenient
method
for
multiple
C(sp3)–H
bond
functionalization
of
saturated
cyclic
amines
through
oxoammonium
salt-promoted
oxidation
to
afford
β-oxo
iminium
ion
as
key
intermediate,
followed
by
cascade
addition
with
thiocyanate
and
diverse
N-,
O-,
S-containing
nucleophiles
in
the
green
solvent
EtOH.
Notably,
chiral
spiro
azapolyheterocycles
were
prepared
enantioselectively
(>20:1
dr,
up
99%
ee)
when
cysteine
or
serine
esters
used
substrates.
Moreover,
concise
late-stage
modification
several
natural
product
derivatives
was
accomplished
using
this
method.
Organic Letters,
Journal Year:
2022,
Volume and Issue:
24(5), P. 1224 - 1227
Published: Jan. 31, 2022
Relatively
unstable
cyclic
imines,
generated
in
situ
from
their
corresponding
alicyclic
amines
via
oxidation
of
lithium
amides
with
simple
ketone
oxidants,
engage
aryllithium
compounds
containing
a
leaving
group
on
an
ortho-methylene
functionality
to
provide
polycyclic
isoindolines
single
operation.
The
scope
this
transformation
includes
pyrrolidine,
piperidine,
azepane,
azocane,
and
piperazines.
